Acetic Anhydride → (E)-3-(3-Acetoxy-4-methoxyphenyl)acrylic acid

HRID 1260379Notes

Reaction equation

HRID 1260379 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[C:17](OC(=O)C)(=[O:19])[CH3:18]>C1COCC1>[C:17]([O:3][C:4]1[CH:5]=[C:6](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 736186Isoferulic Acid

Product 1

HCID 14214114(E)-3-(3-Acetoxy-4-methoxyphenyl)acrylic acidYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.40 g, 58 mmol) was added portionwise to a solution of (E)-3-(3-hydroxy-4-methoxy-phenyl)-acrylic acid (5.15 g, 26.5 mmol) in THF (100 mL) at 0° C. The resulting mixture was allowed to reach the RT, and acetic anhydride (4 mL, 42.4 mmol) was added. After stirring at reflux temperature for 6 hrs, the reaction mixture was concentrated under reduced pressure. The residue was taken up with AcOEt, and washed with water, aqueous sodium hydrogencarbonate, and brine. The organic layer was then dried over sodium sulphate and evaporated. The resulting raw material was triturated with AcOEt. After filtration and drying, 4.7 g of the title (E)-3-(3-acetoxy-4-methoxy-phenyl)-acrylic acid were obtained, as a white powder.

Workup

  1. additionwas added
  2. temperatureat reflux temperature for 6 hrs
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. washwashed with water, aqueous sodium hydrogencarbonate, and brine
  5. dry with materialThe organic layer was then dried over sodium sulphate
  6. customevaporated
  7. customThe resulting raw material was triturated with AcOEt
  8. filtrationAfter filtration
  9. customdrying

Sources & evidence

ORD record
ord-8116bc13f297404c88961879ba24fb6f
Source dataset
uspto-grants-2013_06
Patent number
US08470831B2

Reaction notes

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